1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59077559, compound

HRID 1359831Notes

Reaction equation

HRID 1359831 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([C:30](O)=[O:31])[C:25]=1[CH3:33])(=[O:12])=[O:11].C1[CH:35]=[CH:36][C:37]2N(O)N=[N:40][C:38]=2C=1.CCN=C=NCCCN(C)C.[CH:55]1([N:58]2CCN[CH2:60][CH2:59]2)C[CH2:56]1>CN(C=O)C>[CH:37]1([CH2:38][N:40]2[CH2:60][CH2:59][N:58]([C:30]([C:26]3[C:25]([CH3:33])=[C:24](/[CH:23]=[C:16]4\[C:17](=[O:22])[NH:18][C:19]5[C:15]\4=[CH:14][C:13]([S:10]([CH2:9][C:3]4[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=4[Cl:8])(=[O:11])=[O:12])=[CH:21][CH:20]=5)[NH:28][C:27]=3[CH3:29])=[O:31])[CH2:55][CH2:56]2)[CH2:36][CH2:35]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 47420041-CyclopropylpiperazineHCID 590775075-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

Product 1

HCID 59077559HCID 59077559, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (200 mg, 0.4 mmol), HOBt (54 mg, 1 eq.) and EDAC (154 mg, 2 eq.) in DMF (1.5 mL) was stirred at rt for 30 mins. To the mixture was added 1-cyclopropyl-piperazine (112 mg, 2 eq.) in DMF (1.5 mL). After stirring at rt for overnight, the precipitate was collected by vacuum filtration, washed with water, sodium bicarbonate and water and dried to give 227 mg (90%) of the titled compound.

Workup

  1. stirringAfter stirring at rt for overnight
  2. filtrationthe precipitate was collected by vacuum filtration
  3. washwashed with water, sodium bicarbonate and water
  4. customdried

Sources & evidence

ORD record
ord-91afd6f07b104de3bb4a6c17172278f4
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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